Allylamine → 5,6-Dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-(2-propenyl)-1H-benzimidazol-2-amine

Participants

Reaction Steps

Following General Procedure V, allylamine (Aldrich, 5 mL, 66.64 mmol), and 2-bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole (250 mg, 0.65 mmol) reacted for 92 h. Purification on a silica gel column with 1:25 methanol:CH2Cl2 gave the title compound (195 mg, 0.54 mmol, 84%); MS (EI): m/z (rel. intensity) 358 (0.05, M+); 1H NMR (DMSO-d6) δ7.41 (s, 1H, Ar—H), 7.36 (s, 1H, Ar—H), 7.10 (t, 1H, NH, J=11.2 Hz), 5.94 (m, 1H, CH), 5.70 (d, 1H, CH, J=6.5 Hz), 5.25 (m, 3H, overlapping OH and CH2), 5.09 (d, 1H, OH, J=8.8 Hz), 4.35 (m, 1H, CH), 3.98 (m, 2H, CH2), 3.92 (m, 1H, CH), 3.81 (m, 1H, CH), 1.38 (d, 3H, CH3, J=6.5 Hz).

Provenance & Evidence